Ethanol → 4-(1-Cyclohexen-1-yl)-3-ethylbenzoic acid

HRID 423308Notes

Reaction equation

HRID 423308 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13]C(C#N)=[CH:9][C:8]=2[CH2:15][CH3:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[OH-:17].[K+].[CH2:19]([OH:21])[CH3:20]>O>[C:1]1([C:7]2[CH:14]=[CH:13][C:20]([C:19]([OH:17])=[O:21])=[CH:9][C:8]=2[CH2:15][CH3:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 593167164-(1-Cyclohexen-1-yl)-3-ethylbenzonitrile

Product 1

HCID 593168044-(1-Cyclohexen-1-yl)-3-ethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(1-cyclohexen-1-yl)-3-ethylbenzonitrile (D17) (824 mg, 3.91 mmol) and potassium hydroxide (2.19 g, 39.1 mmol) in ethanol (36 mL) and water (8 mL) were heated at 90° C. (block temperature) for 20 h. The reaction mixture was concentrated in vacuo and the residue partitioned between ethyl acetate (120 mL) and aqueous hydrochloric acid (2M, 50 mL) before the organic phase was washed with further hydrochloric acid (2M, 50 mL), dried (phase separator) and concentrated in vacuo to give the title compound as a yellow oil (808 mg, 3.51 mmol). δH (methanol-d4, 400 MHz) 7.87 (1H d), 7.76 (1H dd), 7.11 (1H, d) 5.59-5.54 (1H, m), 2.68 (2H, q), 2.25-2.15 (4H, m), 1.84-1.67 (4H, m), 1.20 (3H, t). LCMS (ES): C15H18O2 requires 230; found 229 (M−H+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate (120 mL) and aqueous hydrochloric acid (2M, 50 mL) before the organic phase
  3. washwas washed with further hydrochloric acid (2M, 50 mL)
  4. customdried (phase separator)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0842e7f99d43419cb97f62d5a9082abe
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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